Ertapenem

Class: Beta-lactam (carbapenem)

Spectrum of activity:	Gram-negative
Details of activity:	Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Carbapenems bind to all PBPs, with PBP2 and PBP4 as the highest-affinity targets. Ertapenem is mainly active against Enterobacteriaceae and has a longer half life than othe carbapenems
Description:	Semisynthetic, derived from thienamycin. Longer half live
Institute where first reported:	MSD/Merck
Year first mentioned:	1992
Highest developmental phase:	Approved by FDA in 2001
Development status:	Approved, off-patent

Chemical structure(s):
Canonical SMILES:	C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](C(=O)NC4=CC(=CC=C4)C(=O)O)NC3)C(=O)O
Isomeric SMILES:	C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O
InChI:	InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
InChI Key:	JUZNIMUFDBIJCM-ANEDZVCMSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/150610

External links:
Guide to Pharmacology:	ertapenem
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4867097/
Citations:	https://pubmed.ncbi.nlm.nih.gov/17488146/ https://pubmed.ncbi.nlm.nih.gov/27101841/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6535521/